Most people will tell you to be lit like a UFO, only do it on an internal-hubbed, upright converted mountain bike. Preference should be on button up shirts and jeans.

It would seem that doing this once a week would be doable, trying for 3 round trips, on and on, would become problematic.

Also, if you already are comfortable on the road bike, I'd stick with that.

No matter what, enjoy the ride, do what you think will work specifically for you - and have fun.